Carboxylation and mitsunobu reaction of amines to give carbamates: Retention vs inversion of configuration is substituent-dependent

被引：100
作者：
Dinsmore, CJ [1 ]
Mercer, SP [1 ]
机构：
[1] Merck Res Labs, Dept Med Chem, W Point, PA 19486 USA
来源：
ORGANIC LETTERS | 2004年 / 6卷 / 17期
关键词：
D O I：
10.1021/ol0491080
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mild method for the synthesis of carbamates from amino alcohols involves sequential carboxylation with carbon dioxide, followed by a Mitsunobu reaction. Unexpectedly, the stereochemical course of the Mitsunobu reaction is dependent on whether the carbamic acid intermediate is N-substituted with hydrogen (retention) or carbon (inversion).
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页码：2885 / 2888
页数：4
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